Tris(furan-2-yl)phosphane → methyl 1-(3-chloropyridin-2-yl)-3-{[6-(trifluoromethyl)pyridin-3-yl]methyl}-1H-pyrazole-5-carboxylate
Reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:5]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=2)[N:4]=1.C([Sn](CCCC)(CCCC)[C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[N:28][CH:29]=1)CCC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN1C(=O)CCC1>[Cl:18][C:17]1[C:12]([N:5]2[C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7][C:3]([CH2:2][C:24]3[CH:29]=[N:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[N:4]2)=[N:13][CH:14]=[CH:15][CH:16]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Under argon, 0.8 g (2.36 mmol) of methyl 3-(bromomethyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, 1.18 g (2.60 mmol) of 5-(tributylstannyl)-2-(trifluoromethyl)pyridine, 0.11 g (0.47 mmol) of tri-2-furylphosphine and 0.07 g (0.07 mmol) of tri(dibenzylideneacetone)dipalladium were stirred in NMP at 100° C. for 2 h. The solvent was distilled off under reduced pressure, and the residue was taken up in 80 ml of ethyl acetate and stirred vigorously with 70 ml of saturated potassium fluoride solution for 60 min. The organic phase was separated off, washed once with saturated sodium chloride solution, dried over sodium sulphate and concentrated using a rotary evaporator. The desired product was obtained by chromatographic purification.
Workup
- distillationThe solvent was distilled off under reduced pressure
- customThe organic phase was separated off
- washwashed once with saturated sodium chloride solution
- dry with materialdried over sodium sulphate
- concentrationconcentrated
- customa rotary evaporator
Sources & evidence
- ORD record
- ord-db99f7fc5bbb46798e3a25066bedb5f1
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791139B2
Reaction notes
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